This invention concerns nitroaryl carbonyl compounds, their intermediate nitrodihydroaryl carbonyl compounds, and processes for preparing the nitroaryl carbonyl and nitrodihydroaryl carbonyl compounds.
There are no known references to nitrodihydroaryl carbonyl compounds. E. E. Gol'teuzen et al., Izv. Akad. Nauk. SSSR, Ser. Khim., No. 5, 1083 (1972), discloses related charge-transfer or anionic o complexes derived from 1,3-dinitrobenzene.
Ortho-nitrophenyl and para-nitrophenyl carbonyl compounds are known. Representative of the publications which disclose these types of compounds are: U.S. Pat. No. 3,547,619 (Back); U.S. Pat. No. 3,591,623 (Back); U.S. Pat. No. 3,839,433 (Wasley); U.S. Pat. No. 3,920,839 (Wasley); U.S. Pat. No. 4,309,424 (Martin); U.S. Pat. No. 3,931,225 (Fryer); Hromatka et al., Monatsh. Chem., 100, 469 (1969); Umio et al., Chem. Pharm. Bull. (Tokyo), 17 (3), 605 to 610 (1969); and CA 64: 17522/h.
Preparation of certain o-nitrophenyl carbonyl compounds is known. Germain et al., J. Heterocyclic Chem., 13, 1209 (1976), and Bourdais et al., Tetrahedron Lett. No. 3, 195 (1970), disclose preparation of some o-nitrophenyl carbonyl compounds by reacting halogen-substituted nitrobenzenes with stabilized carbanion species. Garcia et al., J. Heterocyclic Chem., 11, 219 (1974), disclose preparation of some o-nitrophenyl carbonyl compounds from 2-nitrotoluene by reaction with an acetal of N,N-dimethylformamide followed by acylation and hydrolysis of an intermediate enamine. Walsh et al., J. Med. Chem., 25, 446 (1982), disclose preparation of some o-nitrophenyl carbonyl compounds from substituted o-nitrotoluenes by reaction with diethyloxalate and sodium ethoxide, followed by hydrolysis. Geyer et al., J. Med. Chem. 25, 340 (1982), discloses preparation of some o-nitrophenyl carbonyl compounds from 2-(2-nitrophenyl)acetic acids by reaction with benzene in the presence of thionyl chloride and aluminum chloride.
Fused ring nitroaryl carbonyl compounds are very difficult or impossible to prepare by the known processes. Furthermore, none of the known preparations for nitroaryl carbonyl compounds suggests any of the instant processes which comprise reacting a nitroaryl compound with a silane. The processes of the present invention are characterized by being simple to operate and by providing a wide range of products including novel nitrodihydroaryl carbonyl compounds, and novel nitroaryl carbonyl compounds. The nitroaryl carbonyl compounds made by the processes of the instant invention may be converted by conventional chemical methods into useful compounds having pharmaceutical activity.